Yarn treating process and composition therefor



" Patented Feb. 20, 1940 I YARN TREATING PROCESS AND COMPOSI- TION THEREFOR.

Joseph B. Dickey and James G. McNally,'

Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, N. Y.,

New Jersey a corporation of No Drawing. Application November 26, 1937,

. Serial No. 176,684

18 Claims.

This invention relates to the conditioning of textile yarns and more particularly to the conditioning of filaments and yarns composed of organic derivatives of cellulose such as cellu- -5 lose acetate, cellulose acetate propionate, cellulose acetate butyrate; etc, to render them more amenable to" textile operations, and with particular reference to the treatment of cut staple yarns composed of these materials for the purl0 pose of reducing the tendency toward the ac:-

.cumulation of charges of static electricity.

As is well known in the manufacture of yarns, particularly those composed of or containing cellulose organic derivatives, it is necessary to treat l5 theyarn in order to reduce the tendency toward breakage of the individual filaments or fibers when they are subjected to various mechanical strains and to lubricate the yarn in order to facilitate handling in such operations as spinning, twisting, winding and reeling. Itis also necessary to treat yarn to adapt it for use as warp or filling or for the manufacture of various types of knitted fabrics. In knitting, it is par-'- ticularly important that the yarn be soft and 2B pliable in order that it may conform readily to the contour of the needles and thus produce a closely knit fabric free from such defects as stitch distortion, pin holes, laddering, and the like.

30 In addition, especially in operations where the yarns tend to accumulate high charges of static electricity which render them difficult, if not.

ofthe compounds referred to in the prior art is highlvapor pressure. Another drawback is;

that such compounds often have a too drastic solvent action on the yarn. In addition, many of .5 the known de-electrifioation agents are insufliciently soluble in or miscible with the customary yarn lubricants as to preclude their use in connection with yarn lubricating formulas.

This invention has as its principal object to lug agents which are particularly adapted for the treatment of yarns composed of or containing organic derivatives of cellulose. ther object is to provide a new and improved n type of antistatic or lie-electrification agent for necessary to apply to the yarn an antistatic or exampleyone of the drawbacks of a good many manufacture of cut staple fibers.

' J provide an entirely new class of yarn condition-- A furuse-in connection with such yarns. A still further object is to provide a means by which yarns composed of or containing organic derivatives of cellulose may be simultaneously lubricated and tie-electrified. A specific I object of the invention isto provide a method of treating such yarns to adapt them for the manufacture of cut staple class'of hitherto unknown chemical compounds. Other objects will appear hereinafter.

These objects are accomplished by the follow:

ing invention, whichin its broader aspects comprises the discovery that organic and inorganic salts of furan and hydrogenated furan amines having the formula:

a-rinLR'f where R. is a hydrogenated or unhydrogenated furfuryl group, R and R" being the'same as R or hydrogen, alkyl, alkaryl, or aryl, may be used as yarn treating agents and in particular An'additional object is to provide a new as de-electrification'agents either alone or in admixture with animal, mineral, or vegetable oils in the treatment of yarns composed of or containing organic derivatives of cellulose, particularly to adapt such yarns for the manufacture In the above compounds of cut staple fibers.

the alkyl, alkaryl, and aryl groups may be substituted with other groups including hydroxyl', amino, carboxy, etc. The salts, both inorganic and organic are represented by the following formula:

I 4 u I I where X is any inorganic or organic compound having the salt-forming properties with basic organic amines and R, R and B" have the" meaning previously described. We have found that these compounds have marked antistatic orde-electrification properties when applied to cellulose organic derivative'yams and are particularly valuable in preparing such yarns for the we have also found that such compounds may in somecases be employed as yarn softening agents as well asantistatic agents since they are capable of rendering such yarns soft and pliable without at'the same time having too drastic a solvent action thereon. In this connection they are particularly valuable in adapting yarns for various textile operations, particularly knitting and similar operations where it is necessary that the yarn shall be.soft and pliable and easily conformable to the contour of knitting needles or other parts of the textile machinery.

The various organic and inorganic acid salts of these amines may be prepared by methods analogous to those referred to in the prior art. As a rule, we prefer to treat the desired amine with a stoichiometric amount of the desired acid or acids, or in certain cases an excess of the acid may be used. The amines from which these compounds are obtained in accordance with our invention may be prepared according to the procedure outlined by Adkins on page 2056, volume 55 of the Journal of the American Chemical Society. In this connection, however, it is to be noted, that so far as we are aware, the

specific classes of compounds above referred to have never heretofore been prepared.

Typical examples of the compounds which we have found may be used as favorable yarn treating agents in accordance with my invention are: the tetrahydrofurfuryl amine salt of sulfonated olive oil, ditetrahydrofurfuryl amine cetyl sulfate, and ditetrahydrofurfuryl ethyl amine cetyl sulfate. The first of these compounds may be prepared by treating sulfonated olive oil with tetrahydrofurfuryl amine until the residue no longer turns blue litmus red. The second compound may be prepared, for example, by treat ing 32.2 g. of cetyl sulfate with 18.5 g. of ditetrahydrofurfuryl amine. The third compound may be prepared by treating 32.2 g. of cetyl sulfate h 18 g. of ditetrahydrofurfuryl ethyl amine.

In accordance with our invention these com-' pounds may be applied directly to the yarn during or after spinning or may be added to the spinning solution itself. We have found that these compounds have exceptional antistatic or de-electrification properties which enable them to substantially eliminate the tendency of yarns, particularly those composed of or containing organic derivatives of cellulose, such as cellulose acetate, cellulose acetate .propionate, cellulose acetate butyrate, to accumulate static charges of electricity, especially in the manufacture and use of cut staple fibers. These compounds may be employed as antistatic or de-electrification agents with especially valuable results in the manufacture of out staple fibers designed for the manufacture of yarns on the cotton, woolen or worsted systems.

In the following examples and description we have set forth several of the prefered embodiments of our invention, but they are included merely for purposes of illustration and not as a limitation thereof.

Our invention will more readily be understood by reference to the following examples in which typical applications of the invention are set forth.

Example I.Yarn designed for the production of..cut.'.staple fibers and composed of cellulose acetate is treated by applying thereto ditetrahydrofurfurylamine oleate by means of an applicator roll. The amount of the antistatic agent may run from 4 to 25% by weight of the untreated yarn.

Example II.--A conditioning liquid is made up as follows:

Per cent Tetrahydrofurfurylmethoxymethylether a '70 Furfurylmethylamine palmitate 30 and applied to textile materials such silk, wool.

cellulose acetate, etc., as described in Example I. If the yarn is intended primarily for knitting the amount of conditioning liquid applied may vary from 4 t'o25% by weight of the yarn, and if for 1 de-electrification properties which are used as illustrated in Examples I and II.

Example III .A conditioning liquid particularly useful for use on cut staple fibers and which may be used for other textile operations is made up as follows:

. Per cent Tritetrahydrofurfurylamine phosphate 1 Blown olive oil 40 8, 3-tetrahydrofurfuryloxydiethylether 59 Example IV Per cent Tetrahydrofurfurylamine acetate 5 Neats-foot oil 95 Example V I Per cent Tetrahydrofurfurylphenylmethylamine caproate 10 Blown neats-foot oil 60 Tetrahydrofurfuryl lactate 30 Example VI Per cent Tetrahydrofurfurylamine laurate 20 Laurie acid 10 Neat's-foot oil Example VII I Per cent Tetrahydrofurfurylethanolamine stearate 10 Light mineral oil Example VIII Per cent Tetrahydrofurfurylamine mono-cetyl palmitate 50 Blown sperm oil 50 Example IX Per cent Ditetrahydrofurfurylcetylamine cetyl sulfate- 5 Mineral oil 1.

Example X .Per cent Water 80 Gelatin -l 5 Tetrahydrofurfurylamine oleyl sulfate 10 Tetrahydrofurfuryl lactate 5 Example XI Per cent Water '70 Water soluble cellulose ester 5 Difurfurylamine oleatee 20 Sulfonated olive oil 5 As will be apparent from the above examples and description, the conditioning agents of our invention may be applied by a wide variety of methods. For example, we may employ the agent as an ingredient of the spinning dope from which the filaments are formed, the amount of the agent so employed depending upon a number of factors, such as the particular cellulose derivative used in making the yarn, the solvent or solvent combination used in making up the spinning solution, and the degree of softness or pliability desired in the yarn, etc.

If the conditioning agent is to be applied to the yarn after spinning, this may be done by bringing the yarn in contact with a wick, roll, or felt wet therewith or the liquid may be applied by immersion, spray, or otherwise. The

particular point at which the liquid is applied may vary. It may, for example, be applied to the yarn inside or outside the spinning cabinet, between the guide and godet roll, between the godet or other roll or guide and the point of winding and/or twisting. In some cases, the liquid may even be applied to the yarn after winding onto cones, spools, bobbins, or the like or by the socalled bobbin to bobbin method. In the case of staple fiber manufacture, the liquid may be applied to the yarn prior to, or after cutting into staple lengths.

The amount of the agent so employed will vary widely depending upon the results desired, the specific nature of the material to which the agent is applied, the use to which the yarn is eventually to be put and other factors. For example, in a given case where a cellulose organic acid ester yarn such as a yarn composed of cellulose acetate, is intended for knitting, about 4 to 25% or more by weight, based on the weight of the dry yarn, may be satisfactory, while if the yarn is intended for weaving, the amount may vary between about 1 and 5%..

Although in the above examples we have referred primarily to yarn treating compositions containing only the conditioning agent and an oil, other ingredients such as solvent, non-solvents, emulsifying agents, blending agents and the like, may be' added within the scope of our invention. Likewise, various dyes or other coloring matter maybe included in case it is desired to permanently or fugitively tint or dye the material undergoing treatment.

Although we have found it convenient to illustrate our invention by reference to compositions containing specific percentages of the various ingredients, these percentages may vary widely depending upon the particular purpose for which the composition is intended. For example, if it is desired to control the solvent or softening action of the conditioning agent, the amount of the agent may be adjusted, as, for example, by

reducing the amount of the agent and correspondingly increasing the amount of oil or other ingredient. x

While we have described our invention with particular reference to the treatment of yarns composed of organic derivatives of cellulose such as cellulose acetate, the conditioning agents and formulas described herein are applicable to the conditioning of many other types of cellulose derivativeyarns such as those composed of or containing cellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl cellulose and others, as well as to the conditioning of silk, wool, cotton, viscose and other natural or artificial materials.

The term yarn" as used herein and in the claims is to be understood as including a single filament, a plurality of filaments associated into vidual strands of natural or artificial materials,

as well as cut staple fibers produced from natural and/or artificial filaments or threads and spun yarr produced from such staple fibers.

As indicated above, the yarn conditioning agents of our invention are particularly valuable as antistatic agents. Another feature of these compounds is that they are soluble in or misciblewith a wide variety of mineral, blown and unblown, drying and semi-drying animal and vegetable oils such as cottonseed, olive, castor, neatsfoot,-sperm and other oils. This enables them to be used with any of such oils in making up a wide variety of yarn treating formulas of varying composition.

The yarn conditioning method and compositions of our invention possess many outstanding advantages. The fundamental outstanding characteristic of the agents employed and their ability to reduce thatendency of yarns composed of or containing organic derivatives of cellulose to accumulate charges of static electricity in use in various textile operations and particularly in the manufacture of cut staple fibers. Another outstanding characteristic of these compounds is their property of miscibility with or solubility in a wide variety of animal, mineral and vegetable oils and other specfic compounds which are capable of acting as lubricating and softening agents. In addition, due to their solubility in water, they may be readily removed from yarns and fabrics by means of the usual aqueous scour baths. v

What we claim and desire to secure by Letters Patent of the United States is:

1. The process of conditioning yarn to render it more amenable to textile operations including knitting, weaving, spinning, and the like which -comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component a salt of a compound selected from the group consisting of the furan and hydrogenated furan amineshav ing the following formula:

hydrogenated furfuryl groups, hydrogen, alkyl,

alkaryl and aryl groups, and the hydroxy-,-

amino-; and carboxy-substituted alkyl, alkaryl, and aryl groups.

2. The process of conditioning yarn composed of or containing organic derivatives of cellulose to render it more amenable to textile operations including knitting weaving, spinning, and the' like which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening compound a salt of a compound selected from the group consisting of the furan and hydrogenated furan amines having the following formula:

R-N .nx

I wherein X is a compound having salt-forming p operties with basic organic amines, R is an oranic radical selected from the group consisting of hydrogenated and unhydroge'nated furfuryl groups, and R and R" are radicals selected from the group'consisting of hydrogenated and um hydrogenated .furfuryl groups, hydrogen, alkyl,

alkaryl and aryl groups, and the hydroxy-, amino-, and carboxy-substituted alkyl, alkaryl, and aryl groups.

3. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component a salt of a compound selected from the group consisting of the furan and hydrogenated furan amines having the following formula:

softening composition containing as its essential lubricating and softening component a salt of a compound selected from the group consisting of the furan and hydrogenated furan amines having the following formula:

wherein X is a compound having salt-forming properties with basic organic amines, R is an organic radical selected from the group consisting of hydrogenated and unhydrogenated furfuryl groups, and R and R" are radicals selected from the group consisting of hydrogenated and unhydrogenated furfuryl groups, hydrogen, alkyl, alkaryl and aryl groups, and the hydroxy-,

' amino-, and carboxy-substituted alkyl, alkaryl,

and aryl groups, and a textile lubricant.

5. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component ditetrahydrofurfurylamine oleate.

6. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening-component tetrahydrofurfuryl amine acetate.

'7. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning,-and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and. softening component ditetrahydrofurfurylcetylamine cetyl sulfate.

8. A conditioning agent for rendering yarns more amenable to textile operations including knitting, weaving, spinning and the like which comprises a salt of a compound selected from the group consisting of the furan and hydrogenated furan amines having the following formula:

wherein X is a compound having salt-forming properties with basic organic amines, R is an organic radical selected from the group consisting of hydrogenated and unhydrogenated furfuryl groups, and R and R" are radicals selected from the group consisting of hydrogenated and unhydrogenated furfuryl groups, hydrogen, alkyl, alkaryl and aryl groups, and the hydroxy-, amino-, and carboxy-substituted alkyl, alkaryl, and aryl groups.

9. A conditioning agent for rendering textile yarns composed of or containing organic derivatives of cellulose more amenable to textile operations including knitting, weaving, spinning, and

the like which comprises a salt of a compound selected from the group consisting of the furan and hydrogenated furan amines having the following formula:

wherein X is a compound having salt-forming properties with basic organic amines, R is an organic radical selected from the group consisting of hydrogenated and unhydrogenated furfuryl groups, and R and R" are radicals selected from the group consisting of'hydrogenated and unhydrogenated furfuryl groups, hydrogen, alkyl, alkaryl and aryl groups, and the hydroxy-, amino-, and carboxy-substituted alkyl, alkaryl, and aryl groups, and a textile lubricant.

10. A conditioning agent for rendering yarns composed of or containing cellulose acetate more amenable to textile operations including knitting, weaving, spinning, and the like containing ditetrahydrofurfurylamine oleate.

11. A conditioning agent for rendering textile yarns composed of or containing cellulose acetate more amenable to textile operations including knitting, weaving, spinning, and the like, containing tetrahydrofurfurylamine acetate.

12. A conditioning agent for rendering textile yarns composed of or containing cellulose acetate more amenable to textile operations including knitting, weaving, spinning, and the like containing ditetrahydrofurfurylcetylamine cetyl sulfate.

13. Textile yarn amenable to textile operations including knitting, weaving, spinning, and the like impregnated with a lubricant containing a salt of a compound selected from the group consisting of the furan and hydrogenated furan amines having the following formula:

wherein X is a compound having salt-forming properties with basic organic amines, R is an organic radical selected from the group consisting of hydrogenated and unhydrogenated furfuryl groups, and R and R" are radicals selected from the group consisting of hydrogenated and unhydrogenated furfuryl groups, hydrogen, alkyl,

wherein X is a compound having saltforming alkaryl and aryl groups, and the hydroxy-, amino-, and carboxy-substituted alkyl, alkaryl, and aryl groups.

14. Textile yarn composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving, spin ning, and the like, impregnated with a conditioning agent comprising a salt of a compound selected from the group consisting of the furan and hydrogenated furan amines having the following formula:

properties with basic organic amines, B is an organic radical selected from the group consisting of hydrogenated and unhydrogenated iuriuryl groups, and R and R" are radicals selected from the group consisting of hydrogenated and unhydrogenated furfuryl groups, hydrogen, alkyl, alkaryl and aryl groups, and the hydroxy, amino-, and carboxy-substituted alkyl, alkaryl, and aryl groups.

15. Textile yarn composed of or containing organic derivatives of cellulose amenable to ten-= tile operations including knitting, Weaving, spinning, and the like, impregnated with a conditioning agent comprising a salt of a compound selected from the group consisting of the iuran and hydrogenated furan amines having the following formula:

wherein X is a compound having salt-forming properties with basic organicamines, R is an organic radical selected from the group consisting of hydrogenated and unhydrogenated furfuryl groups, and R and R are radicals selected from the group consisting of hydrogenated and unhydrogenated furfuryl groups, hydrogen, alkyl, alkaryl and aryl groups, and the hydroxy-, amino, and carboxy-substituted alkyl, alkaryl, and aryl groups, and a textile lubricant.

16. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a lubricant comprising ditetrahydrofurfurylamine oleate.

17. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a lubricant comprising tetrahydrofurfurylamine acetate.

18. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a lubricant comprising ditetrahydrofuriurylcetylamine cetyl sulfate.

JAMES G. MoNALLY. JOSEPH B. DICKEY. 

